1. Field of the Invention
The present invention relates to novel compounds, particularly novel compounds, which have been extracted and isolated from plants belonging to the family Compositae or plants belonging to the genus Ludwigia of the family Onagraceae, and use of said novel compounds. Further, the present invention relates to use of known compounds, which have been extracted and isolated from plants belonging to the family Compositae or plants belonging to the genus Ludwigia of the family Onagraceae, in pharmaceutical preparations.
2. Description of Related Art
Plants belonging to the family Compositae or plants belonging to the genus Ludwigia of the family Onagraceae, particularly Tithonia diversifolia (Hemsl) A. Gray are known to have pharmacological effects, for example, inhibitory activity against skin diseases (tinea), hepatitis, icterus, and cystitis. For example, Japanese Patent No. 2609780 and Japanese Patent Application No. 127538/1996 propose antidiabetics using a decoction of Tithonia diversifolia (Hemsl) A. Gray or an extract thereof.
Further, compounds isolated from an extract of Tithonia diversifolia (Hemsl) A. Gray are disclosed in literature. For example, Raghwendra Pal, et al. Indian Journal of Chemistry, Section B: Organic Chemical Including Medicinal Chemistry,14B, 259-262 (1976), Raghwendra Pal, et al. Indian Journal of Chemistry, Section B: Organic Chemical Including Medicinal Chemistry, 15B, 208-211 (1977), and Schuster A, et al. Phytochemistry, 31,3139-3141 (1992) disclose, in the order of the documents, compounds represented by general formula (I):
that is, a compound wherein R1 and R2 represent hydroxyl (hereinafter referred to as “TD-7”), a compound wherein R1 represents a hydrogen atom and R2 represents hydroxyl (hereinafter referred to as “TD-9”), and a compound wherein R1 represents a hydrogen atom and R2 represents methoxy (hereinafter referred to as “TD-10”).
Paulo Sergio Pereira, et al. Phytochemistry, 45, 1445-1448 (1997), C. Zdero et al. Phytochemistry, 26, 1999-2006 (1987) discloses compounds represented by general formula (II):
that is, a compound wherein R3 and R4 represent methoxy (hereinafter referred to as “TD-1”) and a compound wherein R3 represents methoxy and R4 represents hydroxyl (hereinafter referred to as “TD-4”).
Baruah Nabin C., et al. Journal of Organic Chemistry, 44, 1831-1835 (1979) discloses a compound represented by general formula (IV):
(hereinafter referred to as “TD-2”).
Baruah Nabin C., et al. Journal of Organic Chemistry, 44, 1831-1835 (1979) discloses a compound represented by general formula (V):
(hereinafter referred to as “TD-8”).
Antonia G. Gonzalez, et al, Journal of Natural Products, 57, 400-402 (1994) discloses(4S,5R)-4-hydroxy-4-[(1E,3R)-3-hydroxy-1-butenyl]-3,3,5-trimethyl1-cyclo-hexanone).
On the other hand, Raghwendra Pal., et al. Journal of Pharmaceutical Science, 65, 918-920 (1976) reports that Tagitinin A to F have been isolated from an extract of Tithonia diversifolia (Hemsl) A. Gray and that, among these compounds, only Tagitinin F had the effect of prolonging the life span of mice in which P388 mouse leukemia was intraperitoneally transplanted. Here Tagitinin A corresponds to TD-7, Tagitinin C corresponds to TD-2, Tagitinin D corresponds to TD-9, and Tagitinin E corresponds to TD-8. However, Tagitinin F does not correspond to TD-1 to 10 according to the invention of this application.
Raghwendra Pal, et al. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 15B, 208-211 (1977) discloses a compound represented by general formula (VI):
(hereinafter referred to as “TD-11”).
Isao Agata, et al. Yakugaku Zasshi, 101, 1067-1071 (1981) discloses a compound represented by general formula (VII):
(hereinafter referred to as “TD-12”).
S. Shibata, et al. Yakugaku Zasshi, 80, 620-624 (1960) discloses a compound represented by general formula (VIII):
(hereinafter referred to as “TD-13”).
Christa Zdero, et al. Phytochemistry, 26, 1999-2006 (1987) discloses a compound represented by general formula (IX):
(hereinafter referred to as “TD-14”).
Unknown compounds, however, are present in plants belonging to the family Compositae or plants belonging to the genus Ludwigia of the family Onagraceae, and identification of these unknown compounds has been desired earnestly. Further, the development of new applications (such as pharmacological effect) of known and unknown compounds, which have been extracted and isolated from these plants, has also be urgently desired.
[Documents]
Patent document 1: Japanese Patent No. 2609780
Patent document 2: Japanese Patent Application No. 127538/1996
Technical Document 1: Raghwendra Pal, et al. Indian Journal of Chemistry, Section B: Organic Chemical Including Medicinal Chemistry, 14B, 259-262 (1976).
Technical Document 2: Raghwendra Pal, et al. Indian Journal of Chemistry, Section B: Organic Chemical Including Medicinal Chemistry, 15B, 208-211 (1977).
Technical Document 3: Schuster A, et al. Phytochemistry, 31, 3139-3141 (1992).
Technical Document 4: Paulo Sergio Pereira, et al. Phytochemistry, 45, 1445-1448 (1997).
Technical Document 5: C. Zdero et al. Phytochemistry, 26, 1999-2006 (1987).
Technical Document 6: Raghwendra Pal, et al. Indian Journal of Chemistry, Section B: Organic Chemical Including Medicinal Chemistry, 15B, 208-211 (1977).
Technical Document 7: Baruah Nabin C, et al. Journal of Organic Chemistry, 44, 1831-1835 (1979).
Technical Document 8: Antonia G. Gonzalez, et al, Journal of Natural Products, 57, 400-402 (1994)
Technical Document 9: Raghwendra Pal, et al. Journal of Phamaceutical Science, 65, 918-920 (1976).
Technical Document 10: Raghwendra Pal, et al. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 15B, 208-211 (1977)
Technical Document 11: Isao Agata, et al. Yakugaku zasshi, 101, 1067-1071 (1981)
Technical Document 12: S. Shibata, et al. Yakugaku Zasshi, 80, 620-624 (1960)
Technical Document 13: Christa Zdero, et al. Phytochemistry, 26, 1999-2006 (1987)